# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shx97
_database_code_depnum_ccdc_archive 'CCDC 1474506'
_audit_update_record             
;
2016-04-16 deposited with the CCDC.
2016-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 O'
_chemical_formula_sum            'C21 H18 O'
_chemical_formula_weight         286.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8626(12)
_cell_length_b                   8.9710(18)
_cell_length_c                   15.298(3)
_cell_angle_alpha                94.01(3)
_cell_angle_beta                 94.00(3)
_cell_angle_gamma                92.42(3)
_cell_volume                     799.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4681
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.624
_exptl_absorpt_correction_T_max  0.798
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean .
_diffrn_standards_number         image
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6576
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         25.34
_reflns_number_total             2905
_reflns_number_gt                1811
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0567P)²+0.0839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2905
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7356(2) 0.14817(19) 0.35785(9) 0.0889(5) Uani 1 1 d . . .
C1 C 0.6871(3) 0.3202(3) 0.51221(14) 0.0777(6) Uani 1 1 d . . .
H1 H 0.8224 0.3327 0.4847 0.093 Uiso 1 1 calc R . .
C2 C 0.6628(4) 0.3973(3) 0.59156(16) 0.0976(8) Uani 1 1 d . . .
H2 H 0.7813 0.4615 0.6172 0.117 Uiso 1 1 calc R . .
C3 C 0.4668(5) 0.3803(3) 0.63262(15) 0.1012(9) Uani 1 1 d . . .
H3 H 0.4509 0.4334 0.6861 0.121 Uiso 1 1 calc R . .
C4 C 0.2923(4) 0.2852(3) 0.59559(14) 0.0927(8) Uani 1 1 d . . .
H4 H 0.1589 0.2730 0.6243 0.111 Uiso 1 1 calc R . .
C5 C 0.3140(3) 0.2069(3) 0.51502(12) 0.0741(6) Uani 1 1 d . . .
H5 H 0.1947 0.1430 0.4898 0.089 Uiso 1 1 calc R . .
C6 C 0.5128(3) 0.2240(2) 0.47251(11) 0.0590(5) Uani 1 1 d . . .
C7 C 0.1706(3) 0.3008(2) 0.21396(13) 0.0676(5) Uani 1 1 d . . .
H7 H 0.0514 0.2653 0.2451 0.081 Uiso 1 1 calc R . .
C8 C 0.1608(4) 0.4397(2) 0.18023(17) 0.0876(7) Uani 1 1 d . . .
H8 H 0.0345 0.4970 0.1888 0.105 Uiso 1 1 calc R . .
C9 C 0.3352(5) 0.4939(3) 0.13432(17) 0.0967(9) Uani 1 1 d . . .
H9 H 0.3274 0.5871 0.1116 0.116 Uiso 1 1 calc R . .
C10 C 0.5201(5) 0.4097(3) 0.12238(15) 0.0876(7) Uani 1 1 d . . .
H10 H 0.6392 0.4457 0.0915 0.105 Uiso 1 1 calc R . .
C11 C 0.5312(3) 0.2716(2) 0.15584(12) 0.0662(5) Uani 1 1 d . . .
H11 H 0.6588 0.2156 0.1474 0.079 Uiso 1 1 calc R . .
C12 C 0.3571(3) 0.21461(19) 0.20155(10) 0.0514(4) Uani 1 1 d . . .
C13 C -0.0065(3) -0.1015(2) 0.21249(13) 0.0646(5) Uani 1 1 d . . .
H13 H -0.0343 -0.0777 0.2708 0.078 Uiso 1 1 calc R . .
C14 C -0.1652(3) -0.1916(2) 0.15952(15) 0.0747(6) Uani 1 1 d . . .
H14 H -0.2972 -0.2282 0.1826 0.090 Uiso 1 1 calc R . .
C15 C -0.1289(4) -0.2269(2) 0.07351(14) 0.0746(6) Uani 1 1 d . . .
H15 H -0.2360 -0.2869 0.0378 0.089 Uiso 1 1 calc R . .
C16 C 0.0662(4) -0.1733(2) 0.04051(13) 0.0764(6) Uani 1 1 d . . .
H16 H 0.0915 -0.1967 -0.0181 0.092 Uiso 1 1 calc R . .
C17 C 0.2266(3) -0.0845(2) 0.09332(11) 0.0645(5) Uani 1 1 d . . .
H17 H 0.3595 -0.0499 0.0700 0.077 Uiso 1 1 calc R . .
C18 C 0.1915(3) -0.04638(18) 0.18074(11) 0.0500(4) Uani 1 1 d . . .
C19 C 0.5468(3) 0.1456(2) 0.38581(11) 0.0603(5) Uani 1 1 d . . .
C20 C 0.3458(3) 0.0620(2) 0.33362(11) 0.0598(5) Uani 1 1 d . . .
H20A H 0.2057 0.1093 0.3475 0.072 Uiso 1 1 calc R . .
H20B H 0.3351 -0.0399 0.3510 0.072 Uiso 1 1 calc R . .
C21 C 0.3677(3) 0.05883(19) 0.23452(10) 0.0512(4) Uani 1 1 d . . .
H21 H 0.5192 0.0227 0.2235 0.061 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.214(2) . ?
C1 C2 1.374(3) . ?
C1 C6 1.387(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.356(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C19 1.487(3) . ?
C7 C12 1.382(2) . ?
C7 C8 1.384(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.362(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(2) . ?
C11 H11 0.9300 . ?
C12 C21 1.521(2) . ?
C13 C18 1.375(2) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(2) . ?
C17 H17 0.9300 . ?
C18 C21 1.525(2) . ?
C19 C20 1.516(2) . ?
C20 C21 1.529(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.0(2) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 118.30(18) . . ?
C5 C6 C19 123.01(17) . . ?
C1 C6 C19 118.68(17) . . ?
C12 C7 C8 120.2(2) . . ?
C12 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 119.3(2) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 121.3(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C7 118.18(18) . . ?
C11 C12 C21 120.54(16) . . ?
C7 C12 C21 121.25(16) . . ?
C18 C13 C14 121.44(18) . . ?
C18 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 120.30(19) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.31(18) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.68(19) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 120.79(18) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 117.48(16) . . ?
C13 C18 C21 123.92(15) . . ?
C17 C18 C21 118.54(15) . . ?
O1 C19 C6 119.68(16) . . ?
O1 C19 C20 120.64(16) . . ?
C6 C19 C20 119.68(16) . . ?
C19 C20 C21 112.45(15) . . ?
C19 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 . . ?
C21 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C12 C21 C18 109.51(13) . . ?
C12 C21 C20 111.57(15) . . ?
C18 C21 C20 113.84(14) . . ?
C12 C21 H21 107.2 . . ?
C18 C21 H21 107.2 . . ?
C20 C21 H21 107.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C19 -179.13(19) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C2 C1 C6 C19 178.9(2) . . . . ?
C12 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C7 -0.7(3) . . . . ?
C10 C11 C12 C21 177.26(16) . . . . ?
C8 C7 C12 C11 0.6(2) . . . . ?
C8 C7 C12 C21 -177.36(15) . . . . ?
C18 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C14 C13 C18 C17 0.0(3) . . . . ?
C14 C13 C18 C21 177.17(17) . . . . ?
C16 C17 C18 C13 0.7(3) . . . . ?
C16 C17 C18 C21 -176.66(16) . . . . ?
C5 C6 C19 O1 -169.4(2) . . . . ?
C1 C6 C19 O1 11.4(3) . . . . ?
C5 C6 C19 C20 10.0(3) . . . . ?
C1 C6 C19 C20 -169.21(17) . . . . ?
O1 C19 C20 C21 -30.3(3) . . . . ?
C6 C19 C20 C21 150.33(17) . . . . ?
C11 C12 C21 C18 -108.83(17) . . . . ?
C7 C12 C21 C18 69.08(19) . . . . ?
C11 C12 C21 C20 124.21(16) . . . . ?
C7 C12 C21 C20 -57.88(19) . . . . ?
C13 C18 C21 C12 -108.2(2) . . . . ?
C17 C18 C21 C12 68.95(19) . . . . ?
C13 C18 C21 C20 17.5(2) . . . . ?
C17 C18 C21 C20 -165.40(16) . . . . ?
C19 C20 C21 C12 -65.50(19) . . . . ?
C19 C20 C21 C18 169.95(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.033
